


The Intern

by kayralyn2414



Category: Supernatural
Genre: Alternate Universe - Office, Anal Fingering, Anal Plug, Anal Sex, Intern Castiel, M/M, Office Sex, Panty Kink, Rimming, Sub Dean Winchester
Language: English
Status: In-Progress
Published: 2014-10-14
Updated: 2014-10-14
Packaged: 2018-02-21 05:25:22
Rating: Mature
Warnings: Creator Chose Not To Use Archive Warnings
Chapters: 1
Words: 1,185
Publisher: archiveofourown.org
Story URL: https://archiveofourown.org/works/2456414
Author URL: https://archiveofourown.org/users/kayralyn2414/pseuds/kayralyn2414
Summary: <blockquote class="userstuff">
              <p>Dean Winchester is your typical office manager, except that he likes wearing panties and subbing for his new intern when the office doors close.</p>
            </blockquote>





	The Intern

Dean wasn’t sure how he could get so lucky. He’s currently getting dressed for work, making sure to put on the panties Cas instructed him to wear today. They’re pink with a big bow on the back, the ribbons hanging down just bellow the swell of his ass, and made of soft cotton.They aren’t big enough to hold in his growing erection, but the tight material makes his perky, round bottom look amazing. Dean examines himself in the mirror, cock getting harder the longer he stares. He needs to finished getting dressed or he is going to have to stop and jack himself off. He knows Cas would be furious if he’s late or if he found out that Dean came in his panties before he had a chance to play with him. He puts on some slacks and he’s off to the office.

When he arrives he sees Cas sitting at his desk outside of Dean’s own office. The intern had only been working for him for two months before he found out Dean’s secret. Dean was the biggest sub Cas had ever met, and he just couldn’t wait to take advantage of that. That’s why shortly after Dean arrives and settles into his chair, he hears a knock at the door before Castiel is entering. 

"Good morning Dean. It’s almost nine o’clock did something keep you busy this morning?" Cas asks, a smirk across his face. 

"Uh, no. Nothing out of the ordinary that is," Dean tries to play it off as if Cas is asking a normal question that holds no underlying meaning. He wouldn’t want his co-workers over hearing anything. 

"Good. You have a meeting today with Michael at eleven, after that you are set to have lunch with a client, Miss Bela Talbot. Will you be needing anything to prepare yourself for these?" Cas asks. To any other unsuspecting worker Dean knows it would sound completely normal. An intern looking to help, get his boss ready for the meetings, find anything he/she may need, etc. Dean knows better than that though.

"Yes, Mr. Novak, there are a few things I could use your assistance with. If you could just close the door, we can get down to business," Dean replies trying to push down the arousal building low in his stomach. 

Cas goes to the door, locking it before turning around and undoing his tie, “I want to see them.” 

There is no stopping the pleasure that shoots straight to his dick. He stands and comes around his desk, his back towards Castiel. With fumbling fingers, he unbuttons his slacks and lets the pants fall past his legs before stepping out of them. He kicks off his shoes and socks and slowly removes his shirt before he places both hands on his desk, leaning over and baring himself to Cas’s inspection. He can feel Cas’s eyes on him and it only makes him harder. His cock twitches in anticipation when he feels hands run over her bare back and slide down to cup his ass through the panties. 

“Beautiful," he hears Cas whisper. With a finger, Cas holds the panties to the side, only to reveal the plug he requested Dean to wear. He tugs lightly at it before pushing it back in, hitting Dean’s prostate. Dean lets out a small whimper, hands gripping his desk tighter as he tries to resist the urge to fuck back on the plug being pulled from his hole again. 

Castiel plays with the toy a few more times before he takes it out; wandering fingers replace where the plug had just been. When he hears Dean’s moans he tuts. “Dean, am I going to have to bring out the cock ring? You know how I feel about you coming before I’ve given you permission,” he says to tease Dean. He knows how much the man can take before it’s too much, Castiel just likes to see him squirm. 

"Nn-no. I can do this, I can be good. Won’t come until you say so, Cas. Pr-promise," Dean chokes out. He can do this, this isn’t the first time Castiel has taken his time, exploring Dean, finding all the right buttons to push to make him go crazy. He trusts Cas, he can be a good sub for him. 

With that confirmation, Castiel continues. He gets to his knees so he can get a better view of the pretty, pink hole on display for him. Moving his fingers to circle it, he watches it flutter under his light touches. Getting tired of light touches, Cas spreads the globes of Dean’s ass apart and leans in to run his tongue over his puckered entrance. Tasting Dean is one of his favorite things to do to the man. Castiel will never get enough of how easily he can slide his tongue past the rim of muscles, how pliant Dean is for him, how the tight, little hole clenches down on his tongue as he fucks into Dean’s ass relentlessly. 

As his jaw starts to acquire a dull ache from the torturous pace he set, he leans back to get a view of his work. When Cas sees Dean’s spit slick hole still clenching, trying to find something to make him feel full again, he almost comes from the sight. How Castiel ever managed to find such a beautiful man, like Dean, he will never know. 

As he stands back up, he runs calloused hands over smooth, freckled skin. Castiel walks around Dean’s desk and reaches into the top drawer for the lube he knows he’ll find there. When Dean looks up to see Cas pulling out the bottle, a shock of arousal runs through him at the prospect of whats to come. 

At this point, he doesn’t care what Cas does to him, as long as he has something to help the feeling of emptiness he feels in his ass. While he hopes that they will actually have time for Cas to fuck him today, Dean knows he’d be happy as long as he got those long fingers in his ass. Besides, Cas’ cock, nothing makes him writhe more and come harder than his fingers, steadily fucking into his hole.

Looking up into Dean’s face, Castiel knows exactly what he wants. They’ve been doing this for a few months now and Cas knows what Dean likes, what gets him off most as well as what Dean would rather stay away from. They’ve experimented with a bunch of different things, and Castiel has a catalog of all of Dean’s favorites stored in his head. Seeing the look in Dean’s eyes now, Castiel knows how much he wants it, and he’s going to give it to him.

As Cas gets back into position behind Dean, he squeezes out a generous amount of lube to coat his fingers. If this is what Dean is looking for, who is Castiel to deny him, Dean’s been good. He’s the best sub he’s ever had, he deserves this, so Cas is going to make him feel better than he ever has.


End file.
